Aluminium lithium tri-tert-butoxide hydride → (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate

HRID 1039667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039667
[C:1]([O:4][CH2:5][C:6](=[O:27])[C@@H:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:19]=[CH:18][C:12]2[O:13][C:14]([CH3:17])([CH3:16])[O:15][C:11]=2[CH:10]=1)(=[O:3])[CH3:2].[Li].CC([O-])(C)C.CC([O-])(C)C.CC([O-])(C)C.[Al+3]>C(O)C>[C:1]([O:4][CH2:5][C@@H:6]([OH:27])[C@@H:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:19]=[CH:18][C:12]2[O:13][C:14]([CH3:16])([CH3:17])[O:15][C:11]=2[CH:10]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 6328594Aluminium lithium tri-tert-butoxide hydrideHCID 67164867(S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate

Produkt 1

HCID 67164253(2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetateAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of (S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate (3270 mg, 8311 μmol) in 100 mL of ethanol was cooled to −78° C. and added to a solution of lithium aluminum tri-tert-butoxyhydride (16623 μl, 16623 μmol) in 45 mL of ethanol at −78 C dropwise via a cannula over 10 minutes. After stirring at −78° C. for 2 hours the reaction was quenched with 25 mL of 1 N HCl and diluted with ethyl acetate (500 mL). The mixture was poured into 200 mL of water, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organics were washed with water, brine, and dried over sodium sulfate and concentrated to provide (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate (3220 mg, 98% yield) as a white solid.

Aufarbeitung

  1. customwas quenched with 25 mL of 1 N HCl
  2. additiondiluted with ethyl acetate (500 mL)
  3. additionThe mixture was poured into 200 mL of water
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  6. washThe combined organics were washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5add6d169bd9414db1345e1de03fe130
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552181B2

Notizen zur Reaktion

Wird geladen…